CHE 1130 Study Guide - Fall 2019, Comprehensive Final Exam Notes - Carbocation, Ion, Hydrogen Chloride

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CHE 1130
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“Things With Rules” Contents
TWR-1
Contents
NOTE: Using our ‘Knowledge Transformation’ approach, ALL Items will REQUIRE a
Redraw step (see bottom).
NOTE: Using our ‘Knowledge Transformation’ approach, Items 1-9 are Property Label steps
(see bottom).
NOTE: Using our ‘Knowledge Transformation’ approach, Item 10 involves the Property
Label, Consequence Label, and Mechanism Label steps (see bottom).
1) Formal Charge: ........................................................................................................................ 2
2) Rules for Drawing Lewis Structures ...................................................................................... 3
3) Shapes of Molecules: Valence Shell Electron Pair Repulsion Theory: ............................... 5
4) Rules for Resonance ................................................................................................................ 8
5) Evaluating Resonance Structures and Estimating Stabilities ............................................. 9
6) Atomic orbitals (AO’s), hybrid atomic orbitals (hAO’s), and molecular
orbitals (MO’s) ....................................................................................................................... 10
7) Determining 1o, 2o, 3o: ........................................................................................................... 13
8) Nomenclature ......................................................................................................................... 14
9) Chapter 5: Stereochemistry .................................................................................................. 15
10) SN1 / SN2 / E1 / E2 .................................................................................................................. 18
The Redraw step: Convert one structural representation to another (e.g. exploded CSF to hash/wedge).
Adding bond dipoles (δ, δ) is an important part of the Redraw step.
The Property Label step: Add easily-deduced information to your Redrawn structure. (Label groups
as ‘top/bottom’, ‘up/down’, ‘cis/trans’, identify 1o, 2o, 3o groups, generate an IUPAC name, etc.)
The Consequence Label step: A Consequence Label is derived from a Property Label by asking ‘so
what?’ Suppose you’ve identified an alky halide as 1o. So what – what are the Consequences of
being a 1o alkyl halide? What is the alkyl halide trying to tell you?
The Mechanism Label step: Use a Consequence Label to decide which reaction mechanism
might be applicable. Then, of course, DRAW the mechanism.
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“Things With Rules” Formal Charge
TWR-2
Formal Charge:
Examples:
Formal charge = starts” owns”
O
C
O O
6 e
-
- (4 lone pair e
-
+ 2 e
-
from bonds)
6 e
-
- (6 lone pair e
-
+ 1 e
-
from bonds)
H C
H
O
H
H C
H
N
H
H H
H
Cl
6 e
-
- (6 lone pair e
-
+ 1 e
-
from bonds)
5 e
-
- (0 lone pair e
-
+ 4 e
-
from bonds)
7 e
-
- (8 lone pair e
-
+ 0 e
-
from bonds)
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